U.S. patent application number 12/957759 was filed with the patent office on 2011-06-02 for sucrose polyesters.
Invention is credited to Donald Benjamin Appleby, Deborah Jean Back.
Application Number | 20110129592 12/957759 |
Document ID | / |
Family ID | 43736061 |
Filed Date | 2011-06-02 |
United States Patent
Application |
20110129592 |
Kind Code |
A1 |
Appleby; Donald Benjamin ;
et al. |
June 2, 2011 |
SUCROSE POLYESTERS
Abstract
Disclosed herein are compositions that include a blend of
sucrose polyesters, wherein each sucrose polyester includes a
sucrose moiety and a plurality of fatty acid ester moieties,
wherein a percentage range of the combined fatty acid ester
moieties of the sucrose polyesters in the blend have a carbon chain
that has trans content.
Inventors: |
Appleby; Donald Benjamin;
(Cincinnati, OH) ; Back; Deborah Jean; (Cleves,
OH) |
Family ID: |
43736061 |
Appl. No.: |
12/957759 |
Filed: |
December 1, 2010 |
Related U.S. Patent Documents
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Application
Number |
Filing Date |
Patent Number |
|
|
61265373 |
Dec 1, 2009 |
|
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Current U.S.
Class: |
426/631 ;
426/442; 426/658 |
Current CPC
Class: |
C07H 13/08 20130101;
A23D 9/013 20130101; A23L 33/26 20160801; A23D 7/011 20130101 |
Class at
Publication: |
426/631 ;
426/658; 426/442 |
International
Class: |
A23G 3/42 20060101
A23G003/42; A23G 1/40 20060101 A23G001/40 |
Claims
1. A composition comprising a blend of sucrose polyesters, wherein
each sucrose polyester comprises a sucrose moiety and a plurality
of fatty acid ester moieties, wherein: a. from about 90% to about
100% of the sucrose polyesters in the blend are selected from a
group consisting of octa-, hepta-, and hexa-sucrose polyesters; b.
from about 25% to about 50% of the combined fatty acid ester
moieties of the sucrose polyesters in the blend comprise a carbon
chain that contains trans content; and c. from about 60% to about
100% of the combined fatty acid ester moieties of the sucrose
polyesters in the blend comprise a C.sub.18 carbon chain, with the
balance of the fatty acid ester moieties of the sucrose polyesters
in the blend comprising a carbon chain independently selected from
C.sub.12-C.sub.17 or C.sub.19-C.sub.22 carbon chains.
2. A composition according to claim 1, wherein about 40% to about
90% of the combined fatty acid ester moieties of the sucrose
polyesters in the blend comprise an unsaturated carbon chain.
3. A composition according to claim 1, wherein the carbon chains
that contain a trans content are C.sub.18 carbon chains selected
from a group consisting of C.sub.18:1 trans, C.sub.18:2 trans, and
combinations thereof.
4. A composition according to claim 1, wherein the fatty acid ester
moieties are derived from an edible oil comprising at least one
trans fatty acid.
5. A composition according to claim 4, wherein the fatty acid ester
moieties are derived from an oil selected from a group consisting
of rapeseed oil, tallow oil, coconut oil, babassu oil, corn oil,
lard, olive oil, peanut oil, sesame oil, soybean oil, canola oil,
palm oil, sunflower oil, safflower oil, cottonseed oil, and
combinations thereof.
6. A composition according to claim 1 comprising: a. from about 60%
to about 99%, based on the total weight of the sucrose polyester
blend, of sucrose polyesters having a complete melting point of
less than about 40.degree. C.; and b. from about 1% to about 40%,
based on the total weight of the sucrose polyester blend, of
sucrose polyesters having a complete melting point of from about
40.degree. C. to about 100.degree. C.; wherein the composition
exhibits a thixotropic area of from about 50,000 to about 300,000
pascals/second at 33.3.degree. C.
7. A composition according to claim 1 comprising, based on the
total weight of the sucrose polyester blend, from about 0% to about
0.5% penta-sucrose polyesters.
8. A composition according to claim 1, wherein the sucrose
polyester blend comprises, based on total weight of the sucrose
polyester blend, a Solid Fat Index of: a. from about 45% to about
75% solids at 10.degree. C.; b. from about 5% to about 25% solids
at 30.degree. C.; and c. from about 5% to about 10%, solids at
40.degree. C.
9. A process of making the composition according to claim 1,
comprising a step of transesterifying a sucrose molecule with an
ester, the ester being produced via esterifying a hydrogenated oil
that comprises a trans fatty acid content of from about 25% to
about 50% with a lower alcohol.
10. A process of making the composition according to claim 1,
comprising a step of transesterifying a sucrose molecule with a
hydrogenated oil that comprises a trans fatty acid content of from
about 25% to about 50%.
11. A process according to claim 10, wherein the oil comprises an
edible oil.
12. A process according to claim 10, wherein the oil comprises an
oil selected from a group consisting of rapeseed oil, tallow oil,
coconut oil, babassu oil, corn oil, lard, olive oil, peanut oil,
sesame oil, soybean oil, canola oil, palm oil, sunflower oil,
safflower oil, cottonseed oil, and combinations thereof.
13. A process of making the composition according to claim 1,
comprising the steps of: a. partially hydrogenating an oil or
methyl ester derived from an oil to produce an oil or methyl ester
comprising carbon chains having a trans fatty acid content of from
about 25% to about 50%; and b. transesterifying a sucrose molecule
with the oil or methyl ester comprising carbon chains having a
trans fatty acid content of from about 25% to about 50% to produce
an esterified sucrose molecule comprising carbon chains having a
trans fatty acid content of from about 25% to about 50%.
14. A food product comprising the composition of claim 1 and at
least one food ingredient.
15. A food product according to claim 14, wherein the food product
comprises, based on total weight of the food product, from about 1%
to 99% of the sucrose polyester blend.
16. A food product according to claim 14, wherein the at least one
food ingredient is selected from a group consisting of cocoa
powder, cocoa butter, chocolate liquor, sugar, non-calorie
sweetener, partially or wholly non-digestible carbohydrate bulking
agent, triglycerides, emulsifiers, water, fresh egg, sugar, flour,
non-pre-gelatinized starch, egg solids, protein solids, flavorings,
colorants, and mixtures thereof.
17. A food product according to claim 14, wherein the food product
is chocolate.
18. A method of providing a reduced fat content food product having
an improved mouth feel comprising a step of incorporating the
composition of claim 1 into a food product.
19. A method according to claim 18, wherein the food product is
chocolate.
Description
CROSS REFERENCE TO RELATED APPLICATION
[0001] This application claims priority to U.S. Provisional
Application Ser. No. 61/265,373, filed Dec. 1, 2009.
FIELD OF THE INVENTION
[0002] The instant invention relates to sucrose polyester
compositions, products comprising such compositions, as well as
methods of making and using such compositions and products.
BACKGROUND OF THE INVENTION
[0003] Sucrose polyesters, because of their bulk and shape, form
different crystalline structures having melting profiles that are
quite dissimilar to certain natural fats and oils. Typically,
sucrose polyesters meeting the compositional restrictions of
Olestra.RTM., as approved by the United States Food and Drug
Administration, have a very flat melting profile across a broad
temperature range.
[0004] By hydrogenating sucrose polyesters, it is possible to
increase the melting point by converting sucrose polyesters
containing unsaturated carbon chains into sucrose polyesters
containing saturated carbon chains; however, the melting profile of
such sucrose polyesters remains flat, resulting in a high solids
content at body temperatures (approximately 37.degree. C.). When
these sucrose polyesters are incorporated into food products, such
a high solids content causes an undesirable, waxy mouth feel for
the consumer eating the food product. This is particularly
disadvantageous when the sucrose polyesters are incorporated into
chocolate or other confections because such products are favored by
the consumer, in part, due to a particular mouth feel associated
with these types of products. In other words, certain food products
(e.g., chocolates, frostings, icings, etc.) may be particularly
preferred because of the products' ability to melt in a consumer's
mouth. Thus, there remains a continuing need for a fat substitute
that can be incorporated into food products, wherein the fat
substitute provides a consumer with a desired mouth-feel when
eating the food products.
SUMMARY OF THE INVENTION
[0005] Sucrose polyester compositions, products comprising such
compositions, as well as methods of making and using such
compositions and products, are disclosed.
[0006] In one embodiment, the present disclosure provides for a
composition comprising a blend of sucrose polyesters, wherein each
sucrose polyester comprises a sucrose moiety and a plurality of
fatty acid ester moieties, wherein from about 90% to about 100% of
the sucrose polyesters in the blend are selected from a group
consisting of octa-, hepta-, and hexa-sucrose polyesters, from
about 25% to about 50% of the combined fatty acid ester moieties of
the sucrose polyesters in the blend comprise a carbon chain that
contains trans content, and from about 60% to about 100% of the
combined fatty acid ester moieties of the sucrose polyesters in the
blend comprise a C.sub.18 carbon chain, with the balance of the
fatty acid ester moieties of the sucrose polyesters in the blend
comprising a carbon chain independently selected from
C.sub.12-C.sub.17 or C.sub.19-C.sub.22 carbon chains.
[0007] In another embodiment, the present disclosure provides for a
process of making the above detailed sucrose polyesters that
includes the step of transesterifying a sucrose molecule with an
ester, the ester being produced via esterifying a hydrogenated oil
that comprises a trans fatty acid content of from about 25% to
about 50% with a lower alcohol.
[0008] In another embodiment, the present disclosure provides for a
food product that includes a sucrose polyester and at least one
food ingredient.
[0009] In yet another embodiment, the present disclosure provides
for a method of providing a reduced fat content food product having
an improved mouth feel comprising the step of incorporating sucrose
polyester into a food product.
DETAILED DESCRIPTION OF THE INVENTION
[0010] As used herein, the articles "a" and "an" when used in a
claim, are understood to mean one or more of what is claimed or
described.
[0011] As used herein, the terms "include", "includes" and
"including" are meant to be non-limiting.
[0012] As used herein, the term "comprising" means various
components conjointly employed in the preparation of the
compositions of the present disclosure. Accordingly, the terms
"consisting essentially of" and "consisting of" are embodied in the
term "comprising".
[0013] As used herein, the "complete melting point" means the
temperature at which the last visible traces of solids disappear.
The complete melting point of a given composition or component is
measured in accordance with AOCS Method Cc 1-25 (American Oil
Chemists' Society).
[0014] As used herein, the term "lower alcohol" means a C.sub.1,
C.sub.2, C.sub.3, or C.sub.4 alcohol, and combinations thereof.
[0015] As used herein, the term "melting point" means the
temperature at which a component starts to change from the solid to
the liquid phase.
[0016] As used herein, the term "octa-sucrose polyester," means
that eight of the available hydroxyl moieties on a sucrose molecule
are esterified with a fatty acid; the term "hepta-sucrose
polyester" means that seven of the available hydroxyl moieties on a
sucrose molecule are esterified with a fatty acid; the term
"hexa-sucrose polyester" means that six of the available hydroxyl
moieties on a sucrose molecule are esterified with a fatty acid;
the term "penta-sucrose polyester" means that five of the available
hydroxyl moieties on a sucrose molecule are esterified with a fatty
acid.
[0017] As used herein, "Solid Fat Content" or "SFC" means the
percentage of a fat or oil that exists in crystalline form at a
given temperature.
[0018] As used herein, the Solid Fat Index, or "SFI" is an
empirical measure of solid fat content (SFC) at standardized
temperature check points.
[0019] As used herein, the term "sucrose polyester" means
compositions comprising sucrose and fatty acids with at least five
of the available hydroxyl moieties on a sucrose molecule esterified
with a fatty acid.
[0020] As used herein, all tests and measurements, unless otherwise
specified, are made at 25.degree. C.
[0021] The test methods disclosed in the Test Methods Section of
the present application should be used to determine the respective
values of the parameters of Applicants' inventions.
[0022] Unless otherwise noted, all component or composition levels
are in reference to the active portion of that component or
composition, and are exclusive of impurities, for example, residual
solvents or by-products, which may be present in commercially
available sources of such components or compositions.
[0023] All percentages and ratios are calculated by weight unless
otherwise indicated. All percentages and ratios are calculated
based on the total composition unless otherwise indicated.
[0024] It should be understood that every maximum numerical
limitation given throughout this specification includes every lower
numerical limitation, as if such lower numerical limitations were
expressly written herein. Every minimum numerical limitation given
throughout this specification will include every higher numerical
limitation, as if such higher numerical limitations were expressly
written herein. Every numerical range given throughout this
specification will include every narrower numerical range that
falls within such broader numerical range, as if such narrower
numerical ranges were all expressly written herein.
[0025] All documents cited are, in relevant part, incorporated
herein by reference; the citation of any document is not to be
construed as an admission that it is prior art with respect to the
present invention.
[0026] To be useful in chocolates and other confections (e.g.,
coatings, frosting, fillings, icings, baked goods, candy and other
food products), non-caloric fat substitutes are ideally solid at
room temperature but have a melting point near or at body
temperature. The melting point and melting profile of the
non-caloric fat substitutes utilized in chocolates and other
confections contribute to the desired mouth-feel associated with
these types of food products. Ideally, the non-caloric fat
substitutes will contain little to no solids at body temperature
(about 37.degree. C.). As stated above, a problem in the art as it
relates to employing particular embodiments of sucrose polyesters
in these types of food products is the ability to provide a food
product that delivers to the consumer a desired mouth feel.
[0027] Applicants have further recognized that the process by which
sucrose polyesters are made may influence the melting profile.
Specifically, Applicants have recognized that sucrose polyesters
made by using fats/oils that have been hydrogenated before
formation of the sucrose polyester do not have the same solid fat
index as sucrose polyesters that are hydrogenated after formation
of the sucrose polyester.
[0028] Disclosed herein are sucrose polyesters having a melting
profile such that the sucrose polyesters provide consumers a
desired mouth feel suited for chocolate, confections, or other like
food products. Processes of making such sucrose polyesters, and
food compositions comprising such sucrose polyesters, are also
disclosed.
Sucrose Polyester:
[0029] Disclosed herein are compositions comprising a blend of
sucrose polyesters, wherein each sucrose polyester comprises a
sucrose moiety and a plurality of fatty acid ester moieties,
wherein: [0030] a. from about 90% to about 100%, or from about 95%
to about 100%, by weight, of the sucrose polyesters in the blend
are selected from a group consisting of octa-, hepta-, and
hexa-sucrose polyesters; [0031] b. from about 25% to about 50%, or
from about 40% to about 50%, or from about 40% to about 45%, by
weight, of the combined fatty acid ester moieties of the sucrose
polyesters in the blend comprise a carbon chain that contains trans
content; and [0032] c. from about 60% to about 100%, or from about
75% to about 95%, or from about 85% to about 90%, by weight, of the
combined fatty acid ester moieties of the sucrose polyesters in the
blend comprise a C.sub.18 carbon chain, with the balance of the
fatty acid ester moieties of the sucrose polyesters in the blend
comprising a carbon chain independently selected from
C.sub.12-C.sub.17 or C.sub.19-C.sub.22 carbon chains.
[0033] In one aspect, from about 40% to about 90%, or from about
50% to about 85%, or from about 60% to about 70%, or about 75%, by
weight, of the combined fatty acid ester moieties of the sucrose
polyesters in the blend may comprise an unsaturated carbon
chain.
[0034] In one aspect, the carbon chains that contain a trans
content may be C.sub.18 carbon chains selected from a group
consisting of C.sub.18:1 trans, C.sub.18:2 trans, and combinations
thereof.
[0035] In one aspect, the composition may comprise a fatty acid
ester derived from an edible oil comprising at least one trans
fatty acid. In one aspect, the edible oil comprising a trans fatty
acid may be selected from rapeseed oil, tallow oil, coconut oil,
babassu oil, corn oil, lard, olive oil, peanut oil, sesame oil,
soybean oil, canola oil, palm oil, sunflower oil, safflower oil,
cottonseed oil, and combinations thereof.
[0036] In one aspect, the composition may exhibit a thixotropic
area of from about 50,000 to about 300,000, or from about 100,000
to about 200,000 pascals/second at 33.3.degree. C., as measured
using the Test Methods described herein. In one aspect, the
composition may exhibit a thixotropic area of from about 50,000 to
about 100,000 pascals/second at 33.3.degree. C., as measured using
the Test Methods described herein.
[0037] In one aspect, the composition may comprise: [0038] a) from
about 60% to about 99%, based on total weight of the sucrose
polyester blend, of a sucrose polyester having a complete melting
point of less than about 40.degree. C., wherein the sucrose
polyester may be liquid at room temperature; and [0039] b) from
about 1% to about 40%, or from about 2% to about 20%, or from about
5% to about 8%, based on total weight of the sucrose polyester
blend, of a sucrose polyester having a complete melting point of
from about 40.degree. C. to about 100.degree. C., or from about
60.degree. C. to about 75.degree. C., wherein the sucrose polyester
may be solid at room temperature.
[0040] In one aspect, the composition may comprise, based on total
weight of the sucrose polyester blend, from about 0% to about 0.5%
penta-sucrose polyesters.
[0041] In one aspect, the composition may have a Solid Fat Index
such that the composition comprises, based on total weight of the
sucrose polyester blend: [0042] a) from about 45% to about 75%, or
from about 65% to about 75%, solids at 10.degree. C.; [0043] b)
from about 5% to about 25%, or from about 15% to about 20%, solids
at 30.degree. C.; and [0044] c) from about 5% to about 10%, or from
about 7% to about 10%, solids at 40.degree. C.
[0045] In one aspect, a process of making a composition as
described herein is disclosed. In one aspect, the process may
comprise a step of transesterifying a sucrose molecule with an
ester, the ester being produced via esterification of a
hydrogenated oil comprising a trans fatty acid content of from
about 25% to about 50%, with a lower alcohol.
[0046] In one aspect, the process may comprise the step of
transesterifying a sucrose molecule with a hydrogenated oil
comprising a trans fatty acid content of from about 25% to about
50%.
[0047] In one aspect, the process may comprise the steps of: [0048]
a.) partially hydrogenating an oil or methyl ester derived from an
oil to produce an oil or methyl ester that comprises carbon chains
having a trans fatty acid content of from about 25% to about 50%;
and [0049] b.) transesterifying a sucrose molecule with said oil or
methyl ester that comprises carbon chains having a trans fatty acid
content of from about 25% to about 50% to produce an esterified
sucrose molecule that comprises carbon chains having a trans fatty
acid content of from about 25% to about 50%.
[0050] Sucrose polyester blends that include sucrose polyesters
that are produced by the processes detailed above may have a
preferred mouth feel when eaten by consumers when compared to post
hydrogenated sucrose polyesters.
[0051] In one aspect, the oil may comprise an edible oil. In one
aspect, the oil may comprise an oil selected from rapeseed oil,
tallow oil, coconut oil, babassu oil, corn oil, lard, olive oil,
peanut oil, sesame oil, soybean oil, canola oil, palm oil,
sunflower oil, safflower oil, cottonseed oil, and combinations
thereof.
[0052] In one aspect, a food composition comprising a sucrose
polyester as described herein and at least one food ingredient is
disclosed. In this aspect, the food composition may comprise a
sucrose polyester, wherein the food composition may comprise, based
on total weight of the food composition, from about 1% to 99%, or
from about 10% to about 90%, or from about 20% to about 80% of a
sucrose polyester composition as described herein. In one aspect,
the food ingredient may be selected from cocoa powder, cocoa
butter, chocolate liquor, sugar, non-calorie sweetener, partially
or wholly non-digestible carbohydrate bulking agent, triglycerides,
emulsifiers, water, egg products, sugar, flour, non-pre-gelatinized
starch, egg solids, protein solids, flavorings, and mixtures
thereof. Exemplary food compositions may include chocolate,
chocolate coatings, baked goods, frostings, candy products, and the
like. In another aspect, sucrose polyesters as described herein may
be employed to deep fry or surface fry food compositions.
[0053] In one aspect, a method of providing a reduced fat content
food product having an improved mouth feel is disclosed, wherein
the method may comprise the step of incorporating a composition as
described above into a food composition. In one aspect, the food
composition is chocolate.
TEST METHODS
[0054] For purposes of the present application, Solid Fat Content;
Trans Content; Thixotropic Area and Fatty Acid Composition are
determined as follows:
Solid Fat Content ("SFC")--A sample of the test composition is
heated to a temperature of 140.degree. F. (60.degree. C.) for at
least 30 minutes or until the sample is completely melted. The
melted sample is then tempered as follows: at 80.degree. F.
(26.7.degree. C.) for 15 minutes; at 32.degree. F. (0.degree. C.)
for 15 minutes; at 80.degree. F. (26.7.degree. C.) for 30 minutes;
and at 32.degree. F. (0.degree. C.) for 15 minutes. After
tempering, the SFC values of the sample at temperatures of
50.degree. F. (10.degree. C.), 70.degree. F. (21.1.degree. C.),
80.degree. F. (26.7.degree. C.), 92.degree. F. (33.3.degree. C.)
and 98.6.degree. F. (37.degree. C.), is determined by pulsed
nuclear magnetic resonance (PNMR) after equilibration for 30
minutes at each temperature. The method for determining SFC values
by PNMR is described in Madison and Hill, J. Amer. Oil Chem. Soc.,
Vol. 55 (1978), pp. 328-31. Measurement of SFC by PNMR is also
described in A.O.C.S. Official Method Cd. 16-81, Official Methods
and Recommended Practices of The American Oil Chemists Society.
3rd. Ed., 1987. Measurement of Trans Content--The trans content, or
trans fatty acid content, as a percentage of the double bonds of
the unsaturated fatty acids in the polyester sample, is determined
by Fourier transform infrared spectrophotometry (FTIR). The FTIR
method used is described in AOCS Official Method Cd 14d-99,
Reapproved in 2009, "Rapid Determination of Isolated trans
Geometric Isomers in Fats and Oils by Attenuated Total Reflection
Infrared Spectroscopy" and is accurate for samples containing equal
to or greater than 1% trans isomer. The trans value obtained by
FTIR, together with the fatty acid composition of the polyester
sample, is used to calculate the ratio of cis:trans double bonds.
Determination of Thixotropic Area--Samples are prepared by
transferring about 8.0 grams of sample into a 57 mm aluminum pan.
The sample is heated to above 113.degree. C. until completely
liquid, then tempered by cooling to 29.degree. C. with agitation.
The sample is then held at 21.degree. C. for 7 days. Using a
suitable cone and plate rheometer (such as Contraves Rheomat 115A,
cone CP-6) maintained at 37.8.degree. C. and capable of measuring
the non-Newtonian flow curve hysteresis for ascending and
descending shear rates programmed from 0 to 800 s-1, the rheometer
is held at 0 s-1 for 120 seconds, then raised to 800 sec-1 in 7.5
minutes, held for 1 s, then decreased to 0 s-1 in 7.5 min to
measure the thixotropic area. The rheometer accuracy is checked
with viscosity standards such as Cannon ASTM Certified Viscosity
Standards, S-2000 and N-350 or equivalent. A sufficient amount of
the test sample is placed on the rheometer plate to fill the gap
between the plate and cone. The thixotropic area is then measured.
Determination of Fatty Acid Composition--The fatty acid composition
of the sucrose polyesters disclosed may be measured by gas
chromatography. First, fatty acid methyl esters of the sucrose
polyesters are prepared via any standard method known in the art
(for example, via transesterification using sodium methoxide), and
then separated on a capillary column (Supelco SP2340, 60.times.0.32
mm.times.0.2 micron), utilizing a Hewlett-Packard Model 6890 gas
chromatograph equipped with a Flame Ionization Detector and a
Hewlett-Packard automatic sampler, Model 7683. The fatty acid
methyl esters are separated by chain length, degree of unsaturation
and isomeric variations including cis, trans and conjugation. The
method is programmed to run for 50 minutes ramping the temperature
from 140-195.degree. C. with and injection temperature of
250.degree. C. and a detection temperature of 325.degree. C. For
calibration, the fatty acid methyl ester reference standard Nuchek
Prep (#446) is used.
EXAMPLES
Example 1
[0055] 20 kilograms of partially hydrogenated soybean oil (Product
No. LP426 available from Golden Brands of Louisville, Ky.) are
placed in a 30 liter reaction vessel equipped with a stirrer and
reflux condenser and reacted with 5375 grams of methanol using
226.6 grams of sodium methoxide as catalyst. The mixture is stirred
at 65.degree. C. for 6 hours; methanol is allowed to reflux. The
reaction mixture is then allowed to rest without stirring until the
glycerin byproduct settles to the bottom of the vessel. The
glycerin layer is then removed and the methyl ester layer is washed
with 10% water by weight of the methyl ester at 30.degree. C. to
remove residual methanol, catalyst, soap and any remaining
glycerin. The wash process is repeated two additional times. The
methyl esters are then dried under vacuum (25 mm Hg) at 95.degree.
C. The methyl esters are then distilled in a wiped film evaporator
at 195.degree. C. and .about.1 mm Hg absolute pressure to separate
the methyl esters from any un-reacted glycerides. The methyl esters
have the following fatty acid composition:
TABLE-US-00001 C.sub.16 12% C.sub.18 10.9% C.sub.18:1 trans 36.4%
C.sub.18:1 cis 29.3% C.sub.18:2 trans 1.6% C.sub.18:2 cis 0.3%
C.sub.18:3 cis 0%
Example 2
[0056] A liquid sucrose polyester sample is prepared using the
methyl ester prepared in Example 1. 1073 grams of the methyl ester
of Example 1, 212 grams of a milled mixture of sucrose and
potassium palmitate and 4.5 grams of potassium carbonate are added
to a 5 liter reaction vessel equipped with overhead mechanical
stirrer, heating mantel and nitrogen sparge tube. The contents of
the reaction flask are heated to 135.degree. C. with vigorous
stirring and nitrogen sparge for .about.3 hours. Another 1073 grams
of the methyl ester of Example 1 is then added along with 4.5 grams
of K.sub.2CO.sub.3. The reaction is continued at 135.degree. C.
until the total conversion of sucrose polyester measures >75%
octa-ester.
[0057] The crude reaction mix from above is then hydrated with
.about.230 mls water and the contents of the flask are allowed to
set without stirring. The top layer (oil layer) is decanted away
from the hydrated soap layer. The oil layer is then dried at
95.degree. C. (25 mm Hg) until free of residual water. The oil
layer is then bleached with 1% Trisyl (available from W.R. Grace)
and pressure filtered to remove the bleaching earth. The treated
oil layer is then passed through a wiped film evaporator to remove
residual methyl esters. The resulting liquid sucrose polyester has
the following properties:
TABLE-US-00002 Sucrose ester distribution Sucrose octa-ester 81.6%
Sucrose hepta-ester 18.1% Sucrose hexa-ester 0.3% Sucrose
penta-ester 0.0% Fatty Acid Composition C.sub.16 12.6% C.sub.18
10.6% C.sub.18:1 trans 36.9% C.sub.18:1 cis 31.8% C.sub.18:2 trans
1.4% C.sub.18:2 cis 0.6% C.sub.18:3 cis 0.3%
Example 3
[0058] 93 grams of the liquid sucrose polyester from Example 2 are
combined with 7 grams of a solid sucrose polyester having a melting
point of 65.degree. C. to give a sucrose polyester blend. The solid
sucrose polyester has the following properties:
TABLE-US-00003 Sucrose ester distribution of the solid Component
Sucrose octa-ester 78.9% Sucrose hepta-ester 21.0% Sucrose
hexa-ester 0.2% Sucrose penta-ester 0.0% Fatty Acid Composition of
the Solid Component C.sub.16 1.5% C.sub.18 3.9% C.sub.18:1 cis 8.3%
C.sub.18:2 cis 3.0% C.sub.20:0 6.8% C.sub.22:0 76%
[0059] The resulting sucrose polyester blend (comprising the liquid
sucrose polyester from Example 2 and the above detailed solid
sucrose polyester) has the following properties:
TABLE-US-00004 Sucrose ester distribution Sucrose octa-ester 80.6%
Sucrose hepta-ester 19.1% Sucrose hexa-ester 0.3% Sucrose
penta-ester 0.0% Fatty Acid Composition C.sub.16 12.4% C.sub.18
10.5% C.sub.18:1 trans 35.1% C.sub.18:1 cis 31.1% C.sub.18:2 trans
3.3% C.sub.18:2 cis 1.7% C.sub.18:3 cis 0.6% C.sub.20 0% C.sub.22
5.3% Thixotropic area: 53,000 Pa/sec @ 33.3.degree. C. SFC
10.degree. C. 64.2% 20.degree. C. 32.5% 30.degree. C. 7.5%
40.degree. C. 5.1%
Example 4
[0060] The properties of the sucrose polyester blend of Example 3
were compared to those of a commercially available sucrose
polyester blend marketed by The Procter & Gamble Company under
the Olean.RTM. brand name. The particular Olean.RTM. product
utilized in this example is produced from partially hydrogenated
soybean oil, in which the hydrogenation conditions are chosen to
minimize the formation of trans fatty acid isomers. The fatty acid
composition and Solid Fat Contents of both samples are compared
below:
TABLE-US-00005 Fatty Acid Sample Blend from Olean .RTM. brand
Composition Example 3 olestra C.sub.16 12.4% 12.7% C.sub.18 10.5%
6.7% C.sub.18:1 trans 35.1% 13.5% C.sub.18:1 cis 31.1% 40.3%
C.sub.18:2 trans 3.3% 3.0% C.sub.18:2 cis 1.7% 17.4% C.sub.18:3 cis
0.6% 0.5% C.sub.20 0% 0.7% C.sub.22 5.3% 3.5% SFC 10.degree. C.
64.2% 10.8% 20.degree. C. 32.5% 7.6% 30.degree. C. 7.5% 6.1%
40.degree. C. 5.1% 5.6% Sucrose ester distribution Sucrose
octa-ester 80.6% 80.5% Sucrose hepta-ester 19.1% 19.2% Sucrose
hexa-ester 0.3% 0.3% Sucrose penta-ester 0% 0% Thixotropic area
53,000 Pa/sec @ 52,000 Pa/sec @ 33.3.degree. C. 33.3.degree. C.
Example 5
[0061] Sucrose polyesters produced on a commercial scale from
soybean oil are hydrogenated to produce a liquid sucrose polyester
fraction with a similar level of unsaturated fatty acids as the
product described in Example 2. When 94 grams of this liquid
fraction is blended with 6 grams of the same solid sucrose
polyester fraction described and utilized in the sample blend of
Example 3, the result is a blend comprising post hydrogenated
sucrose polyesters. The properties of this blend were compared with
the properties of the sucrose polyester blend of Example 3.
TABLE-US-00006 Blend w/Post Fatty Acid Sample Blend from
Hydrogenated Composition Example 3 Sucrose Polyesters C.sub.16
12.4% 12.7% C.sub.18 10.5% 6.7% C.sub.18:1 trans 35.1% 13.5%
C.sub.18:1 cis 31.1% 40.3% C.sub.18:2 trans 3.3% 3.0% C.sub.18:2
cis 1.7% 17.4% C.sub.18:3 cis 0.6% 0.5% C.sub.20 0% 0.7% C.sub.22
5.3% 3.5% SFC 10.degree. C. 64.2% 52.1% 20.degree. C. 32.5% 29.0%
30.degree. C. 7.5% 21.8% 40.degree. C. 5.1% 13.3% Sucrose ester
distribution Sucrose octa-ester 80.6% 78.5% Sucrose hepta-ester
19.1% 21.2% Sucrose hexa-ester 0.3% 0.3% Sucrose penta-ester 0%
0%
Example 6
[0062] 62 g cocoa powder, 173 g whole milk solids, 0.6 g vanillin
and 580 g sucrose are blended. 216 g of the sucrose polyester blend
of Example 3 is added and the mixture is again blended. The blended
mixture is then passed through a Lehman Four-roll Refiner twice
(NIP pressure of 200 psi). Melted chocolate liquor (55 g) is then
added to the refined mixture and then dry conched for 3 hours at
60.degree. C. using a Hobart C-100 mixer set at speed #2. The
temperature is then reduced to 50.degree. C. and 50 g more
Olean.RTM. (High Elaidic version) and 0.6 g lecithin is added. The
mixture is then wet conched at 52.degree. C. for 16 hrs at speed
#1. Another 55 g of the sucrose polyester blend of Example 3 is
added and the blend is cooled to 40.degree. C., poured into molds
and tempered as follows; 10.degree. C. for 16-18 hrs, 15.degree. C.
for 24 hrs, 21.degree. C. for 24 hrs.
Example 7
[0063] 80 g of sucrose and 20 g of the sucrose polyester blend of
Example 3 is mixed at 60.degree. C. 3 g water is then added along
with 0.3 g lecithin. The mixing is continued at 60.degree. C. using
a Hobart C-100 mixer until the water is removed. 26 g of non-fat
dry milk solids are then added along with 12 g of cocoa powder, 3.5
g cocoa butter, and 2 g of the sucrose polyester blend of Example
3. The product is mixed for another 2-3 hours and then 15 g more of
the sucrose polyester of Example 3 is added with 0.4 g lecithin.
The mixing is continued without heating until the product has
cooled to .about.40.degree. C. The mixture is then poured into
molds and tempered as described in Example 6.
Example 8
[0064] 90 g of a commercially available, 85% cacao extra dark
chocolate bar is heated in a double boiler to a complete melt at
125.degree. F. To the melted chocolate, 14.4 g of powdered
confectionary sugar is added and mixed with a spatula. 28.6 g of
the sucrose polyester blend of Example 3 is then added. The mixture
is taken off the double boiler and another 10 g of the commercially
available, 85% cacao extra dark chocolate bar is added to the
mixture and melted into the mixture with stifling until the mixture
cools to 115.degree. F. This step of adding the additional 10 g of
chocolate bar to the mixture is used to "seed" the lipid crystals
to the desired polymorphic form. The chocolate mixture is then
poured into bite size moulds and placed in the refrigerator to
cool. The chocolate mixture hardens upon cooling and is removed
from the moulds.
Example 9
[0065] 90 g of the same commercially available, 85% cacao extra
dark chocolate bar from Example 8 is heated in a double boiler to a
complete melt at 125.degree. F. To the melted chocolate, 14.4 g of
powdered confectionary sugar is added and mixed with a spatula.
28.6 g of the commercially available Olean.RTM. detailed in Example
4 is then added. The mixture is taken off the double boiler and
another 10 g of the commercially available, 85% cacao extra dark
chocolate bar is added to the mixture and melted into the mixture
with stirring until the product cools to 115.degree. F. This step
of adding the additional 10 g of chocolate bar to the mixture is
used to "seed" the lipid crystals to the desired polymorphic form.
The chocolate mixture is then poured into bite size moulds and
placed in the refrigerator to cool. However, the chocolate mixture
in this example did not sufficiently harden to be handled in a
solid form.
Example 10
[0066] 90 g of the same commercially available, 85% cacao extra
dark chocolate bar from Examples 8 and 9 is heated in a double
boiler to a complete melt at 125.degree. F. To the melted
chocolate, 14.4 g of powdered confectionary sugar is added and
mixed with a spatula. 28.6 g of the post hydrogenated sucrose
polyester blend from Example 5 is then added. The mixture is taken
off the double boiler and another 10 g of the commercially
available, 85% cacao extra dark chocolate bar is added to the
mixture and melted into the mixture with stirring until the product
cools to 115.degree. F. This step of adding the additional 10 g of
chocolate bar to the mixture is used to "seed" the lipid crystals
to the desired polymorphic form. The chocolate mixture is then
poured into bite size moulds and placed in the refrigerator to
cool. The chocolate mixture hardens upon cooling and is removed
from the moulds.
Results of Blind Testing for Mouth Feel:
[0067] A blind testing was conducted to evaluate mouth feel
preference between the chocolate prepared in accordance with
Example 8 and the chocolate prepared in accordance with Example 10.
Seven test subjects blindly tasted a sample of the chocolate
prepared in accordance with Example 8 and the chocolate prepared in
accordance with Example 10 and then were asked which chocolate was
preferred for mouth feel, also known as mouth-melting
characteristics. All seven of the test subjects preferred the
chocolate prepared in accordance with Example 8 over the chocolate
prepared in accordance with Example 10 for mouth feel. The test
subjects described the mouth feel characteristics of the chocolate
prepared in accordance with Example 8 as cleaner and less waxy when
compared with the chocolate prepared in accordance with example
10.
[0068] The dimensions and values disclosed herein are not to be
understood as being strictly limited to the exact numerical values
recited. Instead, unless otherwise specified, each such dimension
is intended to mean both the recited value and a functionally
equivalent range surrounding that value. For example, a dimension
disclosed as "40 mm" is intended to mean "about 40 mm."
[0069] Every document cited herein, including any cross referenced
or related patent or application, is hereby incorporated herein by
reference in its entirety unless expressly excluded or otherwise
limited. The citation of any document is not an admission that it
is prior art with respect to any invention disclosed or claimed
herein or that it alone, or in any combination with any other
reference or references, teaches, suggests or discloses any such
invention. Further, to the extent that any meaning or definition of
a term in this document conflicts with any meaning or definition of
the same term in a document incorporated by reference, the meaning
or definition assigned to that term in this document shall
govern.
[0070] While particular embodiments of the present invention have
been illustrated and described, it would be obvious to those
skilled in the art that various other changes and modifications can
be made without departing from the spirit and scope of the
invention. It is therefore intended to cover in the appended claims
all such changes and modifications that are within the scope of
this invention.
* * * * *